I completely relate to your existential jazz journey.  About four years ago I decided to take my love for jazz to the next level: I resolved to become an expert and sought to be a jazz  "activist."  I envisioned educating myself as well as others.  Visions of my future self, a grey haired woman fifty years in the future, was in my mind, speaking at universities, having my own radio show and being known as a trailblazer in the preservation of jazz, the first great American art form.  But alas, with every attempt to gain more knowlege I was confronted with the fact that the jazz is fluid, and like a massive body of water, unlimited.  The more I educated myself, the more I discovered that there was so much I didn't know.  A valuable lesson in life, I suppose.Now I am content with simply listening to the music.  Yes, there are times I hear a tune and find pleasure that I can identify the artist or know what year the song was recorded.  But for now, like you, remaining a dilettante is how I prefer it.